EP0304347B1 - Polysaccharides extraits, notamment, de végétaux utiles comme médicaments et additifs alimentaires - Google Patents
Polysaccharides extraits, notamment, de végétaux utiles comme médicaments et additifs alimentaires Download PDFInfo
- Publication number
- EP0304347B1 EP0304347B1 EP88401774A EP88401774A EP0304347B1 EP 0304347 B1 EP0304347 B1 EP 0304347B1 EP 88401774 A EP88401774 A EP 88401774A EP 88401774 A EP88401774 A EP 88401774A EP 0304347 B1 EP0304347 B1 EP 0304347B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- gossypine
- euphorbine
- polysaccharides
- daltons
- polysaccharide according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/47—Euphorbiaceae (Spurge family), e.g. Ricinus (castorbean)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/807—Poultry or ruminant feed
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/809—Food or edible material: processes, compositions, and products including harvesting or planting or other numerous miscellaneous processing steps
Definitions
- the present invention relates to polysaccharides extracted from plants, as well as methods for their extraction and their application as medicaments and food additives.
- These new polysaccharide substances have the property of increasing the secretion of prolactin, the main lactation hormone, and of increasing the secretion of beta-casein, the main milk protein, and, consequently, increase the secretion of milk in animals and humans, and are therefore susceptible to industrial applications, in particular in animal husbandry and breastfeeding of the human species.
- the present invention relates to polysaccharides containing units corresponding to rhamnose, arabinose, xylose, mannose, galactose and glucose ensuring in animals and humans an increase in the level of plasma prolactin.
- polysaccharides are further characterized in that their molecular mass is between 104 and 106 daltons, in general between 2.104 and 105 daltons.
- These polysaccharides additionally contain nitrogen and sulfur, generally from 1 to 8% nitrogen and from 0.8 to 2% sulfur.
- the invention also relates to methods for preparing these polysaccharides from plants containing these polysaccharides by extraction with hot water, the polysaccharides being recovered from the aqueous extract obtained, the latter possibly being able to be purified.
- the purification can be carried out by all known methods, but in particular it is possible to provide for precipitation of the aqueous extract using organic solvents which are miscible with water and do not dissolve the polysaccharides, in particular the hydroxylated solvents like ethanol, methanol.
- the products according to the present invention are extracts of plants of the genus Gossypium sp. from the Malvaceae family and from the Euphorbia Hirta Linné species from the Euphorbiaceae family.
- the process of the invention essentially consists in treating plant organs of Gossypium sp. , in particular powdered seeds or corresponding oil cakes.
- Gossypium sp. in particular powdered seeds or corresponding oil cakes.
- Euphorbia Hirta the whole plant is reduced to powder.
- the aqueous solution is concentrated and treated in different ways.
- the concentrated aqueous solution is either lyophilized or transformed into a dry powder by physical methods of evaporation and drying.
- the powder thus obtained is then treated either with ethanol, or with methanol, or with other organic solvents which do not dissolve the polysaccharides.
- the aqueous solution of total extracts can also be treated with ethanol or other solvents to precipitate the total polysaccharides.
- the present invention relates more particularly to the highly active polysaccharide fractions, extracted from the genus Gossypium sp. named Gossypine A and Gossypine B.
- Gossypins A and B are characterized as follows: Gossypins A and B are polysaccharides, with a molecular weight between 2.104 - 105 daltons.
- Gossypine A corresponds to the fraction of molecular mass between 2.104 and 5.104 daltons and contains 3.40% ⁇ 0.3 of N and 1.32% ⁇ 0.3 of S.
- Gossypine A By acid hydrolysis, Gossypine A provides monosaccharides which are transformed into alditols by reduction with sodium borohydride. These reduced monosaccharides are acetylated and analyzed by the gas chromatography (GC) technique coupled with mass spectrometry (MS). Gossypine A provides the results (in analyzes by CPG - SM) in percentage of monosaccharides:
- the gas chromatography is carried out according to the following conditions: Glass capillary column 25 m long, 0.32 m / m diameter, film thickness: 0.2 ⁇ m; phase: Silar 10 C, column temperature: 220 ° C, injector temperature: 220 ° C, interface temperature: 250 ° C, helium pressure: 0.7 Bar.
- Mass spectrometry is performed at 70 eV - 0.25 ⁇ A, photomultiplier 1300 eV.
- Gossypine B corresponds to the fraction of molecular mass between 5.104 and 105 daltons and contains 6.7% ⁇ 0.3 of N and 1.32% ⁇ 0.3 of S.
- Gossypine B provides monosaccharides which are analyzed in the form of alditol derivatives, under the same conditions as in the case of Gossypine A.
- Gossypine B analyzed by CPG - SM corresponds to the following percentage of monosaccharides: Rha Macaw Xyl Man Gal Glue acetylated derivative 3.1% 16.3% 6.1% 2.5% 33.9% 33.3% 4.8%
- the present invention also relates to the active, galactogenic fractions extracted from the genus Euphorbia Hirta Linné, called EUPHORBINE A and EUPHORBINE B.
- Euphorbines A and B are characterized as follows: Euphorbines A and B are polysaccharides with a molecular weight between 3.104 and 105 daltons.
- Euphorbine A corresponds to the fraction of molecular mass between 3.104 and 5.104 daltons and contains 3.10% ⁇ 0.3 of N and 1.09% ⁇ 0.3 of S.
- Euphorbine A leads to monosaccharides which are transformed into the reduced form of ose. These reduced monosaccharides are acetylated and analyzed by the gas chromatography technique, coupled with mass spectrometry (CPG-SM).
- Euphorbine A provides the following results: Rha Macaw Xyl Man Gal Glue acetylated derivative 8.4% 19.5% 4.2% 3.8% 19.3% 42.6% 2.2%
- Euphorbine B is a fraction of galactogenic polysaccharide, of molecular mass between 5.104 and 105 daltons and contains 2.5% ⁇ 0.3 of N and 1.1 ⁇ 0.3 of S.
- Euphorbine B leads to monosaccharides which are transformed into the reduced form of ose or alditols.
- the alditols obtained are acetylated and analyzed by the technique (CPG-SM).
- Euphorbine B corresponds to the following results: Rha Macaw Xyl Man Gal Glue acetylated derivative 12.7% 25.1% 9.5% 9.2% 15.8% 19.2% 8.4%
- the products according to the present invention are more particularly advantageous for increasing the level of plasma prolactin in animals or in humans. In mammals they increase the level of beta-casein in the mammary gland.
- galactogenic properties can be used in animal husbandry and in breastfeeding the human species, both in the form of a drug and in the form of a food additive.
- the aqueous phase containing molecules of molecular mass between 3.104 daltons and 105 daltons is then ultrafiltered on a membrane with a threshold of stop of 5.104 daltons. After lyophilization, or nebulization, of these fractions, 8.3 g of Euphorbine A and 2.2 g of Euphorbine B are obtained.
- the fraction of molecular mass less than 5.104 daltons is ultrafiltered on a membrane with a threshold of 2.104 daltons. These various aqueous fractions are lyophilized and thus 295 mg of Gossypine A of molecular mass between 2.104 and 5.104 daltons and 208 mg of Gossypine B of molecular weight between 5.10 5.1 and 105 daltons are obtained.
- Spleens 3 months of age or older are divided into lots of 4 spleens.
- the product to be studied is either in suspension or in solution in 1 ml of water, administered by gavage twice a day for 4 days.
- the mammary glands of the sacrificed animals are removed for the radioimmunoassay of beta-casein (according to the method of FC GREENWOOD, WM HUNTER and JG GLOVER, Bioch. J. (1963) 89, 114).
- Water is administered to the control rats.
- the ratio of the amount of beta-casein produced by the mammary glands of the treated rats to that produced by the mammary glands of the control rats is evaluated.
- the plasma prolactin level is measured in ewes having received, by intravenous injection, test products, using physiological saline as an excipient. Blood samples are taken every 10 minutes for one hour. The plasma obtained by centrifugation is used for the radioimmunoassay of prolactin which is expressed in ng per ml of serum. The sheep are their own witnesses. The plasma prolactin level is measured before and after the injection of the products to be studied.
- results expressed by the ratio between the maximum level of prolactin obtained after the injection and the basic level obtained before the invention, are the following: Dose / day Products
- Prolactin physiological saline (control) 1 500 mg product of example 4
- 300 mg product of example 1 4 100 mg Gossypine A 2
- 100 mg Gossypine B 5 200 mg Euphorbine A 4 50 mg Euphorbine B 5
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Biotechnology (AREA)
- Alternative & Traditional Medicine (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Cephalosporin Compounds (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT88401774T ATE98264T1 (de) | 1987-07-10 | 1988-07-07 | Polysaccharide, extrahiert aus pflanzen und verwendet als medizinen und zusatzstoffe fuer nahrungsmittel. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8709857A FR2617848B1 (fr) | 1987-07-10 | 1987-07-10 | Polysaccharides extraits, notamment, de vegetaux utiles comme medicaments et additifs alimentaires |
FR8709857 | 1987-07-10 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0304347A2 EP0304347A2 (fr) | 1989-02-22 |
EP0304347A3 EP0304347A3 (en) | 1989-03-08 |
EP0304347B1 true EP0304347B1 (fr) | 1993-12-08 |
Family
ID=9353077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88401774A Expired - Lifetime EP0304347B1 (fr) | 1987-07-10 | 1988-07-07 | Polysaccharides extraits, notamment, de végétaux utiles comme médicaments et additifs alimentaires |
Country Status (10)
Country | Link |
---|---|
US (2) | US4948785A (ja) |
EP (1) | EP0304347B1 (ja) |
JP (1) | JPH0657721B2 (ja) |
AT (1) | ATE98264T1 (ja) |
BR (1) | BR8803442A (ja) |
DE (1) | DE3886134T2 (ja) |
DK (1) | DK377888A (ja) |
ES (1) | ES2060666T3 (ja) |
FR (1) | FR2617848B1 (ja) |
IL (1) | IL86881A (ja) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04141064A (ja) * | 1990-10-03 | 1992-05-14 | Sunamiya:Kk | 薬膳調味液、薬膳調味料の製造方法 |
EP0970968A4 (en) * | 1997-03-28 | 2002-01-09 | Kampou Foundation | PHARMACOLOGICALLY ACTIVE SUBSTANCE |
US6254913B1 (en) | 1999-08-27 | 2001-07-03 | Morinda, Inc. | Morinda citrifolia dietary fiber and method |
US6214351B1 (en) | 1999-08-27 | 2001-04-10 | Morinda, Inc. | Morinda citrifolia oil |
US7244463B2 (en) * | 2005-10-18 | 2007-07-17 | Tahitian Noni International, Inc. | Garcinia mangostana L. enhanced animal food product |
US8652546B2 (en) | 2007-09-06 | 2014-02-18 | Tahitian Noni International, Inc. | Morinda citrifolia based formulations for regulating T cell immunomodulation in neonatal stock animals |
US20120237626A9 (en) * | 2000-12-05 | 2012-09-20 | Palu Afa Kehaati | Profiles of lipid proteins and inhibiting HMG-CoA reductase |
US20110217394A1 (en) * | 2000-12-05 | 2011-09-08 | Brett Justin West | Iridoid Based Formulations |
US8574642B2 (en) | 2000-12-05 | 2013-11-05 | Tahitian Noni International, Inc. | Antiviral Morinda citrifolia L. based formulations and methods of administration |
US8790727B2 (en) * | 2000-12-05 | 2014-07-29 | Tahitian Noni International, Inc. | Morinda citrifolia and iridoid based formulations |
US20110171333A1 (en) * | 2000-12-05 | 2011-07-14 | Bryant Wadsworth | Morinda Citrifolia Based Antioxidant and Antimicrobial Formulations for Improved Color Stability and Increased Shelf Life of Various Meat Products |
US20040192761A1 (en) * | 2003-03-25 | 2004-09-30 | Palu Afa Kehaati | Preventative and treatment effects of morinda citrifolia as an aromatase inhibitor |
US7048952B2 (en) * | 2002-05-21 | 2006-05-23 | Morinda, Inc. | Formulation for inhibiting fungal and microbial growth comprising morinda citrifolia puree juice |
US6855345B2 (en) * | 2001-11-02 | 2005-02-15 | Morinda, Inc. | Preventative and treatment effects of Morinda citrifolia on diabetes and its related conditions |
US20070196527A1 (en) * | 2006-02-23 | 2007-08-23 | Jensen Claude J | Preventative and treatment effects of Morinda citrifolia on Osteoarthritis and its related conditions |
WO2002083159A1 (en) * | 2001-04-17 | 2002-10-24 | Morinda, Inc. | Palliative effects of morinda citrifolia oil and juice |
US7070813B2 (en) * | 2001-11-02 | 2006-07-04 | Morinda, Inc. | Preventative and treatment effects of morinda citrifolia as a colon cancer cell growth inhibitor |
US20110160057A1 (en) * | 2001-11-14 | 2011-06-30 | Bryant Wadsworth | Morinda Citrifolia Based Antimicrobial Formulations |
US7442395B2 (en) * | 2002-11-14 | 2008-10-28 | Tahitian Noni International, Inc. | Formulation for treating candidiasis using Morinda citrifolia |
US20060269630A1 (en) * | 2003-04-16 | 2006-11-30 | Palu Afa K | Morinda citrifolia as a 5-Lipoxygenase inhibitor |
US20050106275A1 (en) * | 2003-05-02 | 2005-05-19 | Chen Su | Morinda citrifolia-based formulation for inhibiting metastasis of carcinogenic cells |
JP4073826B2 (ja) * | 2003-06-04 | 2008-04-09 | タヒチアン ノニ インターナショナル インコーポレーテッド | ヤエヤマアオキの抽出物を含む農業用活力剤 |
US20070259060A1 (en) * | 2003-08-12 | 2007-11-08 | Mian-Ying Wang | Formulations and Methods for Treating Breast Cancer with Morinda Citrifolia and Methylsulfonymethane |
US20050260291A1 (en) * | 2004-03-10 | 2005-11-24 | Palu Afa K | Methods and compositions for reactivating acetylcholinesterase |
WO2006028826A2 (en) * | 2004-09-01 | 2006-03-16 | Paulus Wang | Morinda citrifolia-based formulations and methods for weight management |
US20060141076A1 (en) * | 2004-11-01 | 2006-06-29 | Palu Afa K | Morinda citrifolia based compositions and methods for inhibiting xanthine oxidase |
US20060204601A1 (en) * | 2005-03-09 | 2006-09-14 | Palu Afa K | Formulations and methods for preventing and treating substance abuse and addiction |
US20060280818A1 (en) * | 2005-05-26 | 2006-12-14 | Palu Afa K | Nicotinic acetylcholine receptor antagonist |
US20070122507A1 (en) * | 2005-05-26 | 2007-05-31 | Palu Afa K | Histone deacetylase and tumor necrosis factor converting enzyme inhibition |
US20070154579A1 (en) * | 2005-11-29 | 2007-07-05 | Palu Afa K | Morinda Citrifolia Based Formulation And Methods For Weight Management |
US20070237848A1 (en) * | 2005-12-21 | 2007-10-11 | Brad Rawson | MORINDA CITRIFOLIA BASED COMPOSITIONS FOR TREATMENT OF ANTI-INFLAMMATORY DISEASES THROUGH INHIBITION OF COX-1, COX-2, INTERLEUKIN-1beta, INTERLEUKIN-6, TNF-alpha, HLE, AND iNOS |
US20070281903A1 (en) * | 2006-05-04 | 2007-12-06 | Palu Afa K | Morinda Citrifolia-Based Formulation 5-LOX And 15-LOX |
US8535741B2 (en) | 2006-05-12 | 2013-09-17 | Morinda, Inc. | Method and composition for administering bioactive compounds derived from Morinda citrifolia |
US8025910B2 (en) | 2006-05-12 | 2011-09-27 | Tahitian Noni International, Inc. | Method and composition for administering bioactive compounds derived from Morinda citrifolia |
US20080226758A1 (en) * | 2006-11-28 | 2008-09-18 | Shixin Deng | Lipoxygenase and Cyclooxygenase Inhibition |
US20080213415A1 (en) * | 2007-02-08 | 2008-09-04 | Palu Afa K | Treatment of Glaucoma and Diabetic Retinopathy with Morinda Citrifolia Enhanced Formulations |
PT103714B (pt) * | 2007-04-11 | 2020-07-28 | 73100 - Setenta E Três Mil E Cem, Lda. | Processo para a obtenção de um polímero à base de galactose |
US20080317890A1 (en) * | 2007-06-21 | 2008-12-25 | Claude Jarakae Jensen | Method for treating visual impairment through the prophylactic administration of a morinda citrifolia-based naturaceutical |
US20090196944A1 (en) * | 2008-02-01 | 2009-08-06 | Brad Rawson | Methods of Manufacture of Morinda Citrifolia Based Compositions for Treatment of Anti-Inflammatory Diseases through Inhibition of Cox-1, Cox-2, Interleukin -1beta, Interleukin-6, TNF-alpha, HLE, and iNOS |
US8748123B2 (en) | 2009-12-15 | 2014-06-10 | 73100-Setenta e Tres Mil e Cem, Lda. | Fucose-containing bacterial biopolymer |
US20110206786A1 (en) * | 2010-02-23 | 2011-08-25 | Brett Justin West | Acai and Iridoid Based Formulations |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE670523A (ja) * | 1964-10-09 | |||
FR2513518A1 (fr) * | 1981-09-29 | 1983-04-01 | Tubery Pierre | Polysaccharide extrait du gnidia kraussiana, preparation et usages therapeutiques |
HU188311B (en) * | 1982-03-04 | 1986-04-28 | Szendrei,Kalman,Hu | Process for producing biologically active polisaccharide concentrates and pharmaceutical compositions containing them as active agents |
-
1987
- 1987-07-10 FR FR8709857A patent/FR2617848B1/fr not_active Expired - Fee Related
-
1988
- 1988-06-27 IL IL86881A patent/IL86881A/xx not_active IP Right Cessation
- 1988-07-07 DK DK377888A patent/DK377888A/da not_active Application Discontinuation
- 1988-07-07 ES ES88401774T patent/ES2060666T3/es not_active Expired - Lifetime
- 1988-07-07 AT AT88401774T patent/ATE98264T1/de not_active IP Right Cessation
- 1988-07-07 EP EP88401774A patent/EP0304347B1/fr not_active Expired - Lifetime
- 1988-07-07 DE DE88401774T patent/DE3886134T2/de not_active Expired - Fee Related
- 1988-07-08 US US07/216,806 patent/US4948785A/en not_active Expired - Fee Related
- 1988-07-08 JP JP63170752A patent/JPH0657721B2/ja not_active Expired - Lifetime
- 1988-07-08 BR BR8803442A patent/BR8803442A/pt not_active Application Discontinuation
-
1990
- 1990-08-07 US US07/551,492 patent/US5110803A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
BR8803442A (pt) | 1989-01-31 |
EP0304347A3 (en) | 1989-03-08 |
DK377888D0 (da) | 1988-07-07 |
FR2617848A1 (fr) | 1989-01-13 |
DE3886134D1 (de) | 1994-01-20 |
FR2617848B1 (fr) | 1990-01-05 |
US5110803A (en) | 1992-05-05 |
JPH0657721B2 (ja) | 1994-08-03 |
IL86881A0 (en) | 1988-11-30 |
DK377888A (da) | 1989-01-11 |
EP0304347A2 (fr) | 1989-02-22 |
IL86881A (en) | 1992-06-21 |
DE3886134T2 (de) | 1994-04-21 |
ES2060666T3 (es) | 1994-12-01 |
ATE98264T1 (de) | 1993-12-15 |
JPS6431801A (en) | 1989-02-02 |
US4948785A (en) | 1990-08-14 |
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